The first six months of the Esquire fashion director's advice column, tidied up and put together like a whole outfit's worth of sartorial secrets

The first six months of the Esquire fashion director's advice column, tidied up and put together like a whole outfit's worth of sartorial secrets

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Obama wears his suit without a tie. Can I?

Obama wears his suit without a tie. Can I?

So long as you take care to get it right rather than looking as if you just spent the night in a local jail. First up, your collar needs to be more stiff and more formal, with the ability to stand up on its own without the support of a tie. (Softer, lower collars tend to collapse in on themselves when undone.) Similarly, your suit needs to fit without acres of extra cloth flapping about. The rest is all about the way you carry yourself.

Joe Raedle/Getty Images

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Do belts and shoes have to match?

Do belts and shoes have to match?

They need not match exactly — in fact, matching them too closely could look far too try-hard for some tastes — but they should reside in the same ballpark, e.g., chestnut and chocolate are usually close enough, but dark, reddish brown and light tan are not. Needless to say, black and brown should be kept apart, unless they're both so dark that only a lunatic could possibly notice.

Obama wears his suit without a tie. Can I?

So long as you take care to get it right rather than looking as if you just spent the night in a local jail. First up, your collar needs to be more stiff and more formal, with the ability to stand up on its own without the support of a tie. (Softer, lower collars tend to collapse in on themselves when undone.) Similarly, your suit needs to fit without acres of extra cloth flapping about. The rest is all about the way you carry yourself.

Joe Raedle/Getty Images

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Do belts and shoes have to match?

They need not match exactly — in fact, matching them too closely could look far too try-hard for some tastes — but they should reside in the same ballpark, e.g., chestnut and chocolate are usually close enough, but dark, reddish brown and light tan are not. Needless to say, black and brown should be kept apart, unless they're both so dark that only a lunatic could possibly notice.

Jeffrey Westbrook/Studio D

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I spill liquor a lot. What are the best fabrics to wear?

You sound like a social liability. I recommend a neoprene scuba suit. And not dancing with a full glass of hooch in hand. Failing that, try machine-washable clothing (e.g., cotton) and robust weaves like denim, which will stand up to your systematic pattern of abuse.

AFP/Getty Images

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When do you keep on or take off a hat?

The rules governing the doffing of hats are as odd and anachronistic as the people who still insist on wearing them. We do have room, however, for one hard-and-fast rule: Hats should always be removed in public spaces, like the elevators in department stores. (As a sign of respect to the ladies, naturally.) Hat hair goes with the territory. If you suffer, get a shorter haircut or a bigger hat.

AMC

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Are notch lapels okay?

1) George Clooney often wears a notch lapel, so it must be all right, and 2) waiters often wear a notch lapel, so it ain't all right. Somewhere in between the two is the official line that a peak lapel is a sounder, classier bet. What I have more of an issue with is the wing collar. To classicists, a wing is the only good option, but to me, it looks kind of pompous and costumey — on anyone, including Hercule Poirot, but especially on me. An evening shirt with a normal turn-down collar (like the Brooks Brothers one) is more comfortable, physically, morally, and socially, for most of us.

Jeffrey Westbrook/Studio D

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What kind of tie should I wear with a seersucker suit?

Since wearing one is already something of a statement, I suggest toning things down with a plain white button-down oxford shirt and a plain dark silk tie — something of the knit silk variety. Subtle patterns can be good, too, but keep away from stripes that match the width of your seersucker's stripes. It can make the eyes go funny.

Jeffrey Westbrook/Studio D

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Is there a cheap watch that's stylish enough for all eternity?

An accessibly priced watch means quartz driven, and if by "for all eternity" you mean that you plan to hang on to it after you're dead, digital is probably your best bet. Casio's classic G-Shock ($100) has all the robust qualities needed to survive clumsy undertakers. It's no Patek Philippe, but its angular charms work in pleasant counterpoint to dressier outfits — like funeral garb.

Casio

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Can I wear boat shoes with socks?

Listen carefully and no one need get hurt. Step away from the Sperrys (which, by the way, should still be wintering in a bucket of frozen Northeastern seawater to add to their salty patina come spring) and buy some shoes that are actually meant to be worn with socks. Oh, and never put boat shoes and socks in the same sentence again — the best-dressed sailors always go bare ankle.

Elizabeth Griffen/Hearst Digital Media

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If you're bald, is it okay to wear hats in the sun?

Hats are fine. It's only when they are put on people's heads that they become problematic. Fifty years ago, not wearing a hat was a statement; today, wearing a hat is unavoidably a statement. That said, hats perform a valid function in summer. You might opt for a classic panama, a favorite of outdoorsmen like Teddy Roosevelt and famed aviator and Cartier muse Alberto Santos-Dumont. The panama, superlight and comfortable to wear in the stickiest weather, is perfect for wearing with a suit if you must wear a hat at all.

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If not flip-flops in the city, then what?

The beach is one thing, but the sidewalks of New York, with their vague smell of dead body and nonspecific black ooze, are another. Try a pair of low-rise Converse All Stars in canvas. They're natural, can be worn without socks, and, best of all, can be put in the washing machine.